3-(Trifluoromethyl)aniline → HCID 67312238, compound

HRID 2190495Notes

Reaction equation

HRID 2190495 reaction equation
[CH:1]1([C:4]([NH:6][C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)[C:20](O)=[O:21])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1.[F:26][C:27]([F:36])([F:35])[C:28]1[CH:29]=[C:30]([CH:32]=[CH:33][CH:34]=1)[NH2:31].Cl.C(N=C=NCCCN(C)C)C>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:1]1([C:4]([NH:6][C:7]2[O:8][C:9]3[CH:15]=[C:14]([O:16][C:17]4[CH:18]=[C:19]([CH:23]=[CH:24][CH:25]=4)[C:20]([NH:31][C:30]4[CH:32]=[CH:33][CH:34]=[C:28]([C:27]([F:26])([F:35])[F:36])[CH:29]=4)=[O:21])[CH:13]=[CH:12][C:10]=3[N:11]=2)=[O:5])[CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 73753-(Trifluoromethyl)anilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67312850HCID 67312850, compound

Product 1

HCID 67312238HCID 67312238, compoundYield 18.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of 3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)benzoic acid (221 mg, 653 μmol) produced in Example B1(vi) in pyridine (5 mL) were added 3-(trifluoromethyl)aniline (298 mg, 1.85 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (328 mg, 1.71 mmol) and N,N-dimethylpyridine-4-amine (21.6 mmol, 177 μmol), and the mixture was stirred at room temperature for 14 hr. The mixture was concentrated under reduced pressure, and the obtained residue was dissolved in methanol (1 mL) and ethyl acetate (50 mL). This solution was washed with 0.1N hydrochloric acid (50 mL), saturated aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20), and triturated with diisopropyl ether to give the title compound (57.3 mg, 18%) as a pale-brown solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in methanol (1 mL)
  3. washThis solution was washed with 0.1N hydrochloric acid (50 mL), saturated aqueous sodium hydrogencarbonate solution (50 mL) and saturated brine (50 mL)
  4. dry with materialsuccessively, and dried over anhydrous magnesium sulfate
  5. filtrationThe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20)
  8. customtriturated with diisopropyl ether

Sources & evidence

ORD record
ord-1ae3778f85d9410fa692c3ded7f68ca4
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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